title: A unique approach to aldol products for the creation of all-carbon quaternary stereocentres.
abstract: Among the challenges facing asymmetric synthesis the selective construction of quaternary stereogenic centres, particularly those bearing all-carbon substituents, stands out. The aldol reaction has the potential to create such stereocentres, but, despite the many advances in this field, a highly selective and efficient procedure has remained elusive. Here we show that, by choosing an alternative retrosynthetic approach, such products can be prepared in a highly selective fashion. Through the consecutive addition of several organometallic derivatives, an allylzinc reagent is prepared and, on addition to an aldehyde, an aldol-type product is created. The one-pot operation involves the construction of three new carbon-carbon bonds and the formation of an all-carbon quaternary stereocentre. The products of the reaction are amenable to downstream modification, and the procedure should find applications in the fields of natural product synthesis and drug discovery.
authors.affiliation: The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa, 32000 Israel.
authors.forename: Jaya Prakash
authors.initials: JP
authors.lastname: Das
authors.forename: Helena
authors.initials: H
authors.lastname: Chechik
authors.forename: Ilan
authors.initials: I
authors.lastname: Marek
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006868:Hydrolysis; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001688:Biological Products; D002244:Carbon; C116609:3-hydroxybutanal